Holmes Beach, Florida
139 properties available
Walk to the beach (5 min walk) or laze by the backyard pool! Or jump on the free island trolley and see the sights.Step into your tropical "Island Oasis" at Island Interlude & Break! This enchanting retreat caters to up to 12 guests across four bedrooms, ensuring a perfect balance of tranquility and adventure. Immerse yourself in the refreshing poo
Gulf Place 20
Spend all day enjoying bliss on the beach and then retreat to watch the sun setting over the Gulf while sipping a cocktail on your private balcony at this beautiful Holmes Beach condo. Boasting more than 100 feet of deeded beachfront, this Gulf-side community includes additional on-site perks like tennis courts and an outdoor pool. L
Peacock B
This recently updated duplex is your ticket to dreamy Gulf Coast living! This convenient retreat offers a renovated interior and all the home essentials for complete convenience during your stay. Gift shops, golf cart rentals, and great local food-and-drink options are within walking distance. The beach is also just a short stroll from h
La Casa Karen
The resurfacing is necessary due to significant pitting and staining caused when Hurricane Helene filled the pool with sand. Once completed, the pool will look and feel virtually brand new!
Sitting in a privileged location just steps to the beach, this high-end condo in Holmes Beach is just the place for your next vacation! Boasting
North Beach Village 27
This property has a 7-night stay requirement. However, select properties have the flexibility for shorter stays. Let us do the searching for you!
For a relaxing and fun Anna Maria Island vacation, check out this Holmes Beach townhome! A great location and perks like a shared pool guarantee an unforgettable Anna Maria Islan
If you are ready to put your "heels in the sand", look no further. Manna-Tee Beach House is the perfect vacation spot for relaxation on Anna Maria Island. This beautiful 3 bedroom/2.5 bath home located on Holmes Beach on Anna Maria Island has all the amenities for you. Top-of-the-line finishes and fixtures, high ceilings and open-floor plan invites
Welcome to "Come Sail A Bay"! Bring your boat and gear because this newly renovated, pet-friendly, charming single-level home boasts 3 bedrooms and 3 bathrooms, situated on the canal just a few homes away from the open bay! With a minimum stay of 30 nights, "Come Sail A Bay" offers stunning waterfront views the moment you step inside. Recently reno
110 11th Street South - Bradenton Beach - FL 34217No cancellation fees!Cancel 60+ days before arrival → Full refundCancel within 60 days → No refundExtended stays & bookings $20,000+ → Full payment 90 days prior, non-refundable$500 deposit due at booking; balance due 60 days priorThird-party travel insurance through Beach Retreats is non-refundable
Cozy Crab
The best vacation memories are just waiting to be made at this bright home sitting a block from the sand! Pack up the family and make yourself at home at this adorable beach house offering an efficient layout, natural light throughout, and a full kitchen complete with modern appliances. Whether you decide to use each day to simply lounge
Blue Wave Villa East
Welcome to your dream getaway in Holmes Beach, FL! This charming villa is the perfect family-friendly retreat, offering a blend of comfort and convenience just steps away from the stunning beaches. With a heated pool and an inviting patio equipped with comfortable furniture and a gas grill, you can enjoy outdoor dining and rel
NEWLY RENOVATED! In the heart of Holmes Beach on Anna Maria Island rests this charming home just steps to the beaches. This newly remodeled home creates fun Florida island vibes with two bedrooms perfect for a family or a small group getaway. Anna Maria Hideaway lies within a stone's throw from the trolley stops for guests to hop on for a ride and
6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS MADE AFTER 10/10/25 WITH A CHECK-IN DATE AFTER 1/17/26!All Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional $25 per day instead of providing vehicle insuran
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